Old School with Shilo Brooks
Fewer of us than ever are reading books for pleasure. Shilo Brooks is on a mission to change that. Old School is a new podcast from The Free Press about great books and how reading them can make us stronger, better men. The show features intimate conversations with fascinating men—from fitness gurus to philosophers—about the books that shaped their lives. New episodes out every Thursday. Read with us: https://bookshop.org/lists/old-school-with-shilo-brooks
Episodes
February 12, 2026 • 54 mins
Dylan Thomas is one of the 20th century’s legendary poets.
In this episode, English journalist David Aaronovitch joins Shilo to discuss Thomas’ 1954 play Under Milk Wood, a portrait of a small Welsh seaside town, originally produced for radio.
With rich, musical language, Thomas reveals the secret interior lives of the villagers—their dreams, lusts, resentments, and longings—without condescension, inviting the listener to see t...
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February 5, 2026 • 63 mins
Pulitzer Prize–winning playwright David Mamet spent his childhood cutting class and reading at the local library. His first pick was Sinclair Lewis’s Main Street, which he pulled off the shelves at just 11 years old.
Decades later, David thinks the book is terrible, its author “a horrible writer,” and its heroine an insufferable busybody. In this episode, Shilo pushes back, defending the novel and its protagonist.
From there th...
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January 29, 2026 • 52 mins
In this episode, legendary comic Colin Quinn dives into a cult classic that still makes him cry with laughter: John Kennedy Toole’s A Confederacy of Dunces.
The novel follows the misadventures of an overweight, pretentious misanthrope still living with his mother in 1960s New Orleans. It’s a book that turns fart jokes into high art. It’s also, somehow, a love story between a fat incel and a woke activist—a seemingly absurd pairing...
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January 22, 2026 • 48 mins
Dante Alighieri is one of the most consequential poets in human history, and his The Divine Comedy is essential to understanding Western civilization itself. And yet, though most of us have heard of Inferno, Dante remains one of the least read of all the greats. His masterpiece unfolds in three parts—Inferno, Purgatorio, and Paradiso—charting a journey from despair to redemption.
For literature professor Joseph Luzzi, this journe...
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January 15, 2026 • 55 mins
In Venezuela, a U.S. operation that captured President Nicolás Maduro has sent shock waves through the hemisphere. In Iran, a deadly crackdown on nationwide protests has Washington threatening the possibility of direct military action. Meanwhile, war rages on from Ukraine to Sudan. All this instability and conflict makes now a good time to revisit the most acclaimed anti-war novel in American history: Catch-22.
In this episode, El...
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January 8, 2026 • 52 mins
Middlemarch is George Eliot’s (real name Mary Ann Evans) masterpiece. The 900-page Victorian novel is about the people living in a fictional English town in a time of enormous changes.
In this episode, Shilo Brooks sits down with Dominican friar Father Jonah Teller to discuss what makes the book worth reading. Their conversation tackles the novel’s major themes: marriage in all its mismatched forms, political upheaval around ref...
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December 18, 2025 • 41 mins
Richard Dawkins is best known as a formidable evolutionary biologist and biting critic of religion. But when he wants a break from polemics and proofs, he turns to P.G. Wodehouse for a belly laugh.
Wodehouse’s satire skewered British aristocrats, Hollywood phonies, and self-important moralists with surgical precision. In this episode, Shilo Brooks sits down with Dawkins to find out why the British humorist remains one of the shar...
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December 11, 2025 • 64 mins
“If we want things to stay as they are, things will have to change.” This famous line from The Leopard has become a shorthand for moments when a ruling order senses its own looming downfall.
And it feels eerily relevant now, in an age when the liberal order we cherish seems increasingly unsteady. We are living in a moment when we shout “regime decline” from the rooftops. Giuseppe Tomasi di Lampedusa’s classic novel is about what ...
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December 4, 2025 • 62 mins
According to Ryan Holiday, Walker Percy’s The Moviegoer is like the better, more mature cousin to The Catcher in the Rye. In this episode, Shilo Brooks sits down with the author and Daily Stoic founder to discuss the quiet Southern novel set in postwar New Orleans.
The book follows a Korean War veteran who has money, women, and a respectable job but whose inner life is defined by existential malaise and a spiritual itch that he c...
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November 20, 2025 • 62 mins
Most of us have read 1984 or Animal Farm. But fewer know of George Orwell’s first great work—an unvarnished account of his descent into the world of society’s outcasts. In this episode of Old School, Shilo Brooks sits down with Rob Henderson to discuss Down and Out in Paris and London, which is inspired by Orwell’s real-life plunge into the slums of two great European cities.
Henderson draws on his own trajectory from foster care ...
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November 13, 2025 • 61 mins
It’s been 100 years since The Great Gatsby was published. In this episode, Shilo Brooks sits down with journalist Fareed Zakaria to explore why the F. Scott Fitzgerald novel still feels so modern.
Zakaria shares his experience discovering the classic as an Indian immigrant, describing Gatsby as his gateway to understanding America. Together, they unpack the book’s enduring themes: the allure of reinvention and the American dream,...
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November 5, 2025 • 60 mins
Why do we believe what we believe? And how do those beliefs shape our politics?
Thomas Sowell, one of the world’s most influential economists and social philosophers, set out to answer this question in his 1987 book, A Conflict of Visions. In it, he traces the underlying logic behind all modern political divides—why it is that knowing someone’s position on one issue, say gun control, makes it easy to predict their position on a t...
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October 30, 2025 • 57 mins
Carlo Collodi’s The Adventures of Pinocchio is a dark, dazzling Italian fable that is worlds apart from Disney’s sanitized version. Beneath its fantasticism and humor, the story is brimming with poverty, violence, and existential peril. In this episode, Australian rock legend Nick Cave joins Shilo Brooks to talk about one of the best-selling and most widely translated books ever written.
Together, they explore how transgression...
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October 23, 2025 • 54 mins
What is justice? And why should we live justly? These questions lie at the heart of Plato’s Republic, the foundational text of Western philosophy. In building his utopian city, Plato reveals how the quest for perfect justice can slip into tyranny. Yet his call for relentless self-examination—for resisting nihilism and seeking meaning—remains a starting point for us all.
In this episode, Dr. Cornel West joins Shilo Brooks to discus...
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October 16, 2025 • 67 mins
Dr. Mike Israetel is a bodybuilder and scientist who believes reading is as important as a gym session. Steven Pinker’s The Blank Slate changed his life. In this episode, Israetel joins Shilo Brooks to discuss how this explosive book on genetics, human nature, and the myth of infinite potential turned his own outlook (and coaching style) upside down, inspiring humility, killing illusions, and sharpening his science-first approach t...
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October 9, 2025 • 68 mins
Few people have turned a love of the wild into a cultural force quite like Steve Rinella, the outdoorsman and author behind the MeatEater empire. Jim Harrison’s Wolf, published in 1971, changed Rinella’s life. In this episode, Rinella sits down with Shilo Brooks to discuss this stream-of-consciousness novel replete with chaos and male angst. He reflects on growing up in rural Michigan and seeing himself in Harrison’s protagonist—a ...
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October 9, 2025 • 59 mins
Admiral James Stavridis once commanded fleets as Supreme Allied Commander of NATO. Now he commands a collection of 5,000 rare books. Ernest Hemingway’s The Old Man and the Sea changed Stavridis’ life. In this episode, the admiral sits down with Shilo Brooks to discuss the themes of hardship, pride, and resilience that appear in Santiago’s epic struggle at sea. Stavridis, who stuck out in the military for his love of books, and stuc...
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September 22, 2025 • 57 secs
Fewer of us than ever are reading books for pleasure. Shilo Brooks is on a mission to change that. Old School is a new podcast from The Free Press about great books and how reading them can make us stronger, better men. The show features intimate conversations with fascinating men—from fitness gurus to philosophers—about the books that shaped their lives. Coming October 9th.
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